Azanide

Amide anion
Names
Pronunciation	/ˈæzənaɪd/
	IUPAC name Azanide
	Other names Amide; Amide ion; Ammonia ion; Ammonide; Dihydrogen azanide; Dihydrogen nitride; Monoamide;
Identifiers
CAS Number	17655-31-1;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:29337;
ChemSpider	2104824;
PubChem CID	2826723;
CompTox Dashboard (EPA)	DTXSID80385105 ;
	InChI InChI=1S/H2N/h1H2/q-1 Key: HYGWNUKOUCZBND-UHFFFAOYSA-N;
	SMILES [NH2-]; [N-];
Properties
Chemical formula	NH−2
Molar mass	16.023 g·mol−1
Conjugate acid	Ammonia
Structure
Molecular shape	Bent
Related compounds
Other anions	Phosphanide; Arsinide; Imide; Nitride; Nitridohydride;
Related isoelectronic	water, fluoronium
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Azanide is the IUPAC-sanctioned name for the anion NH−2. The term is obscure; derivatives of NH−2 are almost invariably referred to as amides,^[1]^[2]^[3] despite the fact that amide also refers to the organic functional group –C(=O)−NR₂. The anion NH−2 is the conjugate base of ammonia, so it is formed by the self-ionization of ammonia. It is produced by deprotonation of ammonia, usually with strong bases or an alkali metal. Azanide has a H–N–H bond angle of 104.5°.

Alkali metal derivatives

The alkali metal derivatives are best known, although usually referred to as alkali metal amides. Examples include lithium amide, sodium amide, and potassium amide. These salt-like solids are produced by treating liquid ammonia with strong bases or directly with the alkali metals (blue liquid ammonia solutions due to the solvated electron):^[1]^[2]^[4]

2 M + 2 NH₃ → 2 MNH₂ + H₂, where M = Li, Na, K

Silver(I) amide (AgNH₂) is prepared similarly.^[3]

Transition metal complexes of the amido ligand are often produced by salt metathesis reaction or by deprotonation of metal ammine complexes.

References

^ ^a ^b Bergstrom, F. W. (1940). "Sodium Amide". Organic Syntheses. 20: 86. doi:10.15227/orgsyn.020.0086.
^ ^a ^b P. W. Schenk (1963). "Lithium amide". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 1. New York, NY: Academic Press. p. 454.
^ ^a ^b O. Glemser, H. Sauer (1963). "Silver Amide". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry. Vol. 1 (2nd ed.). New York, NY: Academic Press. p. 1043.
^ Greenlee, K. W.; Henne, A. L. (1946). "Sodium Amide". Inorganic Syntheses. Vol. 2. pp. 128–135. doi:10.1002/9780470132333.ch38. ISBN 9780470132333.

[amideNa-1] Bergstrom, F. W. (1940). "Sodium Amide". Organic Syntheses. 20: 86. doi:10.15227/orgsyn.020.0086.

[amideLi-2] P. W. Schenk (1963). "Lithium amide". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 1. New York, NY: Academic Press. p. 454.

[amideK-3] O. Glemser, H. Sauer (1963). "Silver Amide". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry. Vol. 1 (2nd ed.). New York, NY: Academic Press. p. 1043.

[4] Greenlee, K. W.; Henne, A. L. (1946). "Sodium Amide". Inorganic Syntheses. Vol. 2. pp. 128–135. doi:10.1002/9780470132333.ch38. ISBN 9780470132333.

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